Join us for a day filled with delicious sweet treats and an abundance of community fun!
At the Rutland Whoopie Pie Festival, you can enter a competition with other bakers to sell and offer samples of your own whoopie pie recipe.
Please check our FAQs prior to registration if you have any questions.
How it works.
- Deposit: $150 before July 1st, 2026 | $200 after July 1st, 2026.
- Deposit required upon registering – you will receive this back plus $750 if you attend the Festival (received upon check-in).
- You will be paid $750 to set up and provide 250 (3-inch or larger) whoopie pies for sampling at your booth. Each whoopie pie should provide a minimum of four samples.
- No-shows forfeit their deposit and will not be paid.
- All attendees will present a special ticket to receive a sample.
- Festival Ticket Sales begin at 12:00 PM. Ticket Booths will be located at the corner of Merchants Row and Center Street
- You can sell additional whoopie pies and other baked goods.
- A 10 x 10 ft. tent & space will be provided.
- You provide all items needed to set up under the tent (tables, linens, serving utensils, etc.).
- Awards are available for the Overall Best, Most Creative, and People’s Choice Award.
- Judging will be based on texture, appearance, flavor, and creativity.
- Each vendor will be asked to provide 3 whoopie pies, all the same flavor, for the judging contest.
- For People’s Choice Award
- You will collect voting sheets for your booth upon check-in
- The Rutland Whoopie Pie Festival will also have live performances, food trucks, music and day-long activities for the whole family.
- You can collect schedules of events upon check-in for your booth
PLEASE NOTE: Your space is NOT SECURED until you have submitted your deposit (bakers) or space fee (vendors) and you have received confirmation.
Please register your team of bakers by completing the form provided here.


